Unprecedented in Situ Oxidative Ring Cleavage of Isoxazolidines: Diastereoselective Transformation of Nitronic Acids and Derivatives into 3-Hydroxymethyl 4-Nitro Tetrahydrofurans and Pyrrolidines

Nitronic acids undergo an intramolecular 1,3-dipolar cycloaddition to unactivated double bonds, and the resulting isoxazolidines spontaneously evolve by an unprecedented in situ oxidative ring cleavage. The extension of this transformation to silyl nitronates results in a general diastereoselective...

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Veröffentlicht in:	Organic letters 2004-06, Vol.6 (12), p.2027-2029
Hauptverfasser:	Roger, Pierre-Yves, Durand, Anne-Catherine, Rodriguez, Jean, Dulcère, Jean-Pierre
Format:	Artikel
Sprache:	eng
Schlagworte:	Cyclization Furans - chemical synthesis Isoxazoles - chemical synthesis Molecular Conformation Nitro Compounds - chemical synthesis Nitro Compounds - chemistry Oxidation-Reduction Pyrrolidines - chemical synthesis Stereoisomerism
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